Synthesis of Substituted Benzaldehydes via a Two-Step, One-Pot Reduction/Cross-Coupling Procedure

被引：8

作者：

Heijnen, Dorus ^{[1
]}

Helbert, Hugo ^{[1
,2
]}

Luurtsema, Gert ^{[2
]}

Elsinga, Philip H. ^{[2
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands

[2] Univ Groningen, Univ Med Ctr Groningen, Dept Nucl Med & Mol Imaging, Hanzepl 1, NL-9713 GZ Groningen, Netherlands

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 11期

基金：

欧洲研究理事会;

关键词：

REAGENTS;

D O I：

10.1021/acs.orglett.9b01274

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of functionalized (benz)aldehydes, via a two-step, one-pot procedure, is presented. The method employs a stable aluminum hemiaminal as a tetrahedral intermediate, protecting a latent aldehyde, making it suitable for subsequent cross-coupling with (strong nucleophilic) organometallic reagents, leading to a variety of alkyl and aryl substituted benzaldehydes. This very fast methodology also facilitates the effective synthesis of a C-11 radiolabeled aldehyde. Aluminum-ate complexes enable transmetalation alkyl fragments onto palladium and subsequent cross-coupling.

引用

页码：4087 / 4091

页数：5

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